1242149-83-2

Upstream product

• 84459-32-5 2-bromo-5-nitrobenzaldehyde 
• 536-74-3 phenylacetylene 
• 6361-21-3 2-chloro-5-nitrobenzaldehyde 

Downstream Products

• 1338721-83-7 dimethyl 10-nitro-6-phenyl-4-tosyl-3,4-dihydro-2H-pyridazino[6,1-a]isoquinoline-1,1(11bH)-dicarboxylate 
• 1541897-97-5 7-nitro-3-phenylisoquinoline 

Relevant academic research and scientific papers

Synthesis of N-(isoquinolin-1-yl)sulfonamides via Ag2O-catalyzed tandem reaction of ortho-alkynylbenzaldoximes with benchtop stabilized ketenimines

In this project, a moderately efficient approach to multisubstituted N-(isoquinolin-1-yl)sulfonamide derivatives was illustrated, utilizing ortho-alkynylbenzaldoximes and zwitterionic ketenimine salts in a tandem reaction catalyzed by silver oxide. The oxophilicity of Ag2O, along with its nature as Lewis acid, pave the way for a smooth [3 + 2] cycloaddition between isoquinoline N-oxides and ketenimine species, which is a key step in this reaction. DFT calculation suggests that 1,3-dipolar cycloaddition of nitrone and ketenimine proceeds through a selective stepwise mechanism.

Transition-metal-free oxidative cyclization reaction of enynals to access pyrane-2-one derivatives

A novel and efficient metal-free C-H functionalization of enynals is developed to synthesize α-pyrone derivatives via the formation of two C-O bonds. In this project, K2S2O8 has been introduced as an efficient oxygen source and C-H functionalization agent in regioselective oxidative cyclization reaction with a relatively broad substrate scope.

Synthesis of 2-(Isoquinolin-1-yl)prop-2-en-1-ones via Silver(I)-Catalyzed One-Pot Tandem Reaction of ortho-Alkynylbenzaldoximes with Propargylic Alcohols

The silver(I)-catalyzed reaction of ortho-alkynylbenzaldoximes with propargylic alcohols represents a new strategy for the divergent one-pot synthesis of 2-(isoquinolin-1-yl) prop-2-en-1-ones via tandem 6-endo-cyclization, 1,3-dipolar cycloaddition, and intramolecular dehydrative opening of the 2,3-dihydroisoxazole ring. This synthetic protocol tolerates a wide variety of ortho-alkynylbenzaldoximes and propargylic alcohols and affords the corresponding products in excellent yields.

Visible-Light-Promoted Generation of α-Ketoradicals from Vinyl-bromides and Molecular Oxygen: Synthesis of Indenones and Dihydroindeno[1,2-c]chromenes

Ortho-alkynylated α-bromocinnamates can be converted by a visible-light-mediated photocascade reaction with molecular oxygen into either indenones or dihydroindeno[1,2-c]chromenes. The one-step process features key photochemical steps, that is, the initial activation of vinyl bromides through energy transfer to give α-ketoradicals in a reaction with molecular oxygen, followed by α-oxidation of an arene moiety by 6-π electrocyclization, and subsequent hydroxylation by an electron-transfer process from the same photocatalyst leads to the dihydroindeno[1,2-c]chromenes.

Palladium-Catalyzed Copper-Free Sonogashira Coupling of 2-Bromoarylcarbonyls: Synthesis of Isobenzofurans via One-Pot Reductive Cyclization

Palladium-catalyzed copper-free Sonogashira coupling of 2-bromocarbonyls is presented. This method afforded the 2-alkynylaryl carbonyls, useful synthons for the accomplishment of many carbocyclic and heterocyclic motifs. Significantly, the strategy was extended to the one-pot synthesis of isobenzofurans via reduction followed by intramolecular 5- exo -dig cyclization.

A gold(i)-catalyzed intramolecular tandem cyclization reaction of alkylidenecyclopropane-containing alkynes

A novel gold(i)-catalyzed intramolecular tandem cyclization reaction of ortho-(arylethynyl)arenemethylenecyclopropanes provided an efficient approach to prepare functionalized 11H-benzo[a]fluorene derivatives in moderate to good yields. Further transformations as well as applications of the products have been presented and a plausible reaction mechanism has also been proposed on the basis of deuterium labeling and control experiments.

Insights into the Gold-Catalyzed Propargyl Ester Rearrangement/Tandem Cyclization Sequence: Radical versus Gold Catalysis - Myers-Saito- versus Schmittel-Type Cyclization

A detailed study of the gold-catalyzed tandem 1,3-carboxy migration/allene-enyne cycloisomerization was undertaken. It was found that after the initial allene formation the selectivity of the reaction is strongly influenced by the polarization of the remaining alkyne. Depending on the substitution pattern of the starting diynes, either a Schmittel- or a Myers-Saito-type cyclization was triggered. The 6-endo-dig Myers-Saito-type cyclization gave access to benzo[b]fluorenes, while the Schmittel pathway (5-exo-dig) delivered benzofulvenes as final products. In special cases a yet unknown pathway was opened by the ambiphilic nature of the allene moiety. In these cases completely different products were obtained by the nucleophilic attack of the alkyne moiety onto the allene that can also act as an electrophile. Mechanistic studies revealed that diradical pathways can be ruled out for this type of tandem cyclization reactions and it is shown that both steps of the reaction cascade are catalyzed by the gold complex.

Molecular iodine-mediated reaction of 2-(2-phenylethynyl)-Morita-Baylis-Hillman adducts: An easy route to naphthyl ketones and iodo-substituted isochromenes

The molecular iodine-promoted reaction of 2-(2-phenylethynyl)-Morita-Baylis-Hillman adducts is reported. In the presence of I2, naphthyl ketone derivatives are produced, whereas in the presence of I2/K3PO4, iodo-substituted isochromene derivatives are produced. This journal is

Synthesis of substituted isoquinolines via iminoalkyne cyclization using Ag(i) exchanged K10-montmorillonite clay as a reusable catalyst

Monosubstituted isoquinolines are synthesized in good to excellent yields by the Ag(i)-exchanged K10-montmorillonite clay catalyzed ring closure of iminoalkynes. This silver catalyzed ring closure is highly effective in cyclizing aryl- and alkyl-substituted iminoalkynes at 100 °C and accommodates a variety of iminoalkynes, thus affording a convenient route to the synthesis of isoquinolines. The other salient features of this procedure are its reusability, environmentally benign nature, high yield, operational simplicity with fewer steps, easy separation, and minimization of metallic wastes. The reaction proceeds smoothly in moderate yields and tolerates various functional groups. The solid catalyst can be readily recovered and reused. Notably, no additional base or other co-catalysts are needed. A plausible mechanism is proposed in which isoquinolines are formed via simultaneous bifunctional acid-base catalysis by Ag(i) clay. the Partner Organisations 2014.

Solution-phase parallel synthesis of a diverse library of 1,2-dihydroisoquinolines

Synthesis of a 105 membered library of 1,2-dihydroisoquinolines is described. The 1,2-dihydroisoquinoline compounds have been prepared in good yields using a Lewis acid and organocatalyst-cocatalyzed multicomponent reaction of 2-(1-alkynyl)benzaldehydes,